Did They Or Didn’t They??? 15 Alleged Hollywood Hook-Ups

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Updated May 14th, 2012

Celebrities are known for having a good time, but what happens when that “good time” includes a fellow celebrity?

You get our list of 15 alleged hollywood hook-ups.  From Nas and Amy Winehouse to Kobe Bryant and Trina, check out the list below.

Ray J and Whitney Houston (RIP)

Getty: John Gichigi

Reports surfaced in 2007, that Brandy’s brother was dating (late singer) Whitney Houston.

Their alleged fling raised eyebrows considering that Houston is over 20 years older than the R&B singer.

Amy Winehouse and Nas (RIP)

Getty: Sylvia Linares

Amy Winehouse and Nas were spotted in London earlier this year leaving Damian Marley’s birthday party.

The photos sparked controversy considering Winehouse previously recorded a song titled “Me And Mr. Jones” allegedly about her love for the rapper.

Getty: Prince Williams

Gucci Mane and Mya were spotted at Atlanta’s Velvet Room night club in 2009, in seemingly compromising positons.

Mya quickly shot down romance rumors herself however, telling DJ Whoo Kid,

“That was a rumor as well that I had to laugh at. No diss, but the way people turn things around. I’d taken a photo with him at a club and I went to say bye, my manager was present and I went to say by to Gucci and I said something in his ear but I had to get closer because the club music was so loud, they caught me in the wrong pose looking like we had just finished kissing or that we were kissing.”

Getty: Prince Williams

Amber Rose And Chris Brown

Photo Credit: mrsgrapevine.com

Rumors swirled that Amber Rose and Chris Brown hooked up in 2009 at Diddy’s White Party, while she was still with Kanye.
Several people claimed to confirm the rumor by posting pictures of the pair talking at the event including Chris Brown’s good friend Teyana Taylor who said they were “cupcakin it all night.”

Photo Credit: earsucker.com

50 Cent And Paris Hilton

Getty: Jamie McCarthy

50 Cent and Paris Hilton were spotted looking mighty cozy in Las Vegas back in 2007 before the MTV Video Music Awards.

Getty: Jason Merritt

The G-Unit head has denied ever being involved with the heiress and later sparked controversy by telling her to “Get the f*ck off the stage” during one of his performances, allegedly making her cry.

Getty: Arnold Turner

Around the same time Ray-J was spotted with Whitney Houston, the R&B singer and sextape star was seen with Lil Kim.

The “Wait A Minute” collaborators were spotted by TMZ cameras in 2007 entering a party hand in hand.

Getty: bossip.com

Drake and Rihanna

Getty: Johnny Nunez

Drake and Rihanna reportedly hooked up in 2009 at New York’s Lucky Strike bowling alley.

Drake initially denied reports of their hookup saying, “It’s not like that at all.”I’m being honest. [She's] just a friend, that’s all. A great artist.”

He then went on to pen “Fireworks” about their hookup that famed May night.

Getty: Kevin Winter

Kim Kardashian and Kanye  

THEY ARE NOW OFFICIALLY DATING!!! Click HERE to see!

Getty: Noel Vasquez

There were reports in 2010 that the real reason why Kim Kardashian and her boyfriend Reggie Bush broke up was because she cheated with Kanye West.

Kardashian went on to call the rumors “completely false” but has since been spotted with West taping for an episode of “Keeping Up With The Kardashians” an according to In Touch magazine,

“Kanye had his arm around her all evening! He was rubbing her knee all night – they definitely looked like a couple.”

Photo Credit: carltonjordan.com


Rihanna And Kanye

Getty: Kevin Mazur

In 2008 Star Magazine reported that Rihanna and Kanye were spotted kissing backstage at a T.I. concert.

“Rihanna was sitting on Kanye’s lap, singing along to the music. Before long, the two were full-on kissing each other. People were shocked. After a while, Rihanna must have realized people were watching, because she had her security escort her back to the dressing room.”


Amber Rose and Reggie Bush

Photo Credit: live.drjays.com

In 2010 rumors circulated that Amber Rose had moved on from Kanye West and was hooking up with NFL star Reggie Bush.

The ex-girlfriend of Ye and ex-boyfriend of Kim Kardashian were reportedly spotted at the EPSYs getting mighty cozy, where a reported lap dance took place.

HollywoodLife reports,

“The 27-year-old socialite and model, who broke up with rapper Kanye West earlier this month after dating for two years, grabbed Reggie’s hand, stared deeply into his eyes and began to give the athlete a sensual lap dance. Although there was music playing in the background, Amber moved to her own beat and Reggie loved every second of it.”


Trina and Kobe

Photo Credit: hellobeautiful.com and bossip.com

In 2009 there were reports of an alleged altercation between rapper Trina and Vanessa, the wife of Kobe Bryant sparked by a line where the femcee said,

“This n*gga thinkin’ I’m sweatin’ his Rolex watch, you need more than that, to get in my thighs. A car that’s fly, maybe a house in the sky, I know you wanna beat it up right quick, And I was the first b*tch Kobe cheated on his wife with…”

Trina later went on to deny sleeping with Bryant and released a statement saying the rap was “fabricated.”

Photo Credit: hotnewsonglyrics.com

Wale And Solange

Photo Credit: upyourstyle.com

In 2009, DMV rapper Wale made headlines after declaring his love for Beyonce’s little sister.

The two were known to flirt on Twitter before being spotted out together at Central Park.

Following that, he told Honey Magazine,

“I do love her, we’re friends. She’s amazing. She’s a good person. Any single mother contributing to society the way she does — I got a lot of love for them.”


Photo Credit: gossips-celebrity.com


Khloe Kardashian And Jeezy

Photo Credit: gossiponthis.com

In 2008 there were reports that the youngest Kardashian was booed up with Young Jeezy.

The two were spotted partying in Vegas for her 24th birthday alongside her family, Reggie Bush, Lauren London and the Haqq twins from “ATL.”

Photo Credit: therundown.tv

Diddy And Sienna Miller

Photo Credit: theboxhouston.com

Shortly after Diddy’s twin daughters were born, there were reports that he was hooking up with actress Sienna Miller.

TMZ cameras caught the mogul entering a hotel room with Miller and described the surprised look on his face saying,

“Diddy, father of newborn twins, was spotted dropping off Miller at her NYC hotel this morning after a rumored night of partying together in the city. Diddy had a trapped rat look when he noticed cameras watching from across the street — and we’re told a bodyguard was sent over to the photographer to try and get him to delete the footage.”

Photo Credit: exesandhos.tumblr.com


Amber Rose And Fabolous

Photo Credit: Johnny Nunez

Rumors circulated in October that Kanye’s ex-girlfriend had moved on to Fabolous and was pregnant with his baby.

Both Amber and Fab have denied the rumors of being involved and expecting.

Amber took to her Twitter account to say,

“Whoa…Lol I’m NOT Pregnant…Please ppl the internet is 97% wrong ABOUT ME…I’m not THAT girl they portray me to be.”

Fabolous also chimed in on Twitter saying,

“I see Media Takeout is the urban CNN.. Despite the rumor I didn’t get anyone pregnant.. #ItAintMineTweet”

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